• Question: Why might someone want to get away from Chicago for a day?
  • Answer: Even with all Chicago has to offer, sometimes it just feels right to get away for a day.
  • Question: What types of experiences can be enjoyed during a day trip from Chicago?
  • Answer: Exploring a sleepy river town, fishing in a river surrounded by towering canyon walls, skiing, or answering the call of your inner history buff, can leave you feeling relaxed and refreshed.

Best Time for Day Trips from Chicago, Illinois

  • April to June – Ideal for mild weather, blooming gardens, and outdoor adventures.
  • September to October – Perfect for vibrant fall foliage, scenic drives, and fewer crowds.
  • July & August – Warm summer days great for beach trips, hiking, and exploring nearby towns.
  • November – Enjoy cooler weather and quieter visits to historical and cultural sites.
  • December to March – Cold but festive for holiday markets, cozy retreats, and museum visits.

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1. Milwaukee (1 hour 35 minutes)


Explore local breweries and walk along the lakefront on a quick trip.

Milwaukee (1 hour 35 minutes)

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  • Why is Milwaukee known for beer?
    • Thanks to the well-known 1960s Schlitz beer jingle, pop culture fans recognize it as the "beer that made Milwaukee famous." Today, Milwaukee’s German brewing heritage is alive and well, featuring numerous microbreweries, historical brewery tours, and brewpubs alongside farm-to-table eateries serving local craft beers.
  • What is Milwaukee’s connection to Harley-Davidson?
    • Milwaukee is home to the legendary Harley-Davidson, which offers museum tours showcasing motorcycle artifacts, including the oldest-known Harley in the world.
  • Why is Milwaukee called the "City of Festivals"?
    • Also known as the "City of Festivals," Milwaukee hosts over two dozen celebrations, including Summerfest, the world’s biggest music festival.
  • What unique attractions does Milwaukee offer?
    • Milwaukee is home to 75 golf courses, 25 theaters, and 150 parks, making it a great destination for recreation and entertainment.

2. Holland, Michigan (2 hours 30 minutes)


Visit Dutch-inspired shops and stroll tulip-lined streets in spring.

Holland, Michigan (2 hours 30 minutes)

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  • Why is Holland, Michigan a popular destination?
    • There are many reasons to visit Holland, Michigan, but the Dutch heritage experience is the most famous attraction.
  • Where can visitors see tulips in Holland, Michigan?
    • During spring, over 4.5 million tulips bloom across the city, including at Veldheer Tulip Gardens, Windmill Island Gardens, and other locations.
  • What is the Tulip Time Festival?
    • Held in early May, the Tulip Time Festival draws visitors from around the world to enjoy Dutch food, music, parades, and Klompen dancing.
  • What Dutch cultural attractions can visitors experience year-round?
    • At any time, visitors can explore historical Dutch architecture, windmills, Dutch cuisine, the DeKlomp Wooden Shoe & Delft Factory, and a collection of art at the Holland Museum.
  • What is the Dutch Winterfest?
    • Late November brings the Dutch Winterfest, featuring the Parade of Lights, a dazzling holiday event.

3. Kettle Moraine State Forest (2 hours 40 minutes)


Hike scenic trails and bike through rolling hills on a fall weekend.

Kettle Moraine State Forest (2 hours 40 minutes)

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  • What is Kettle Moraine State Forest?
    • Kettle Moraine State Forest is a 30,000-acre forested area in Wisconsin, offering a vast expanse of natural beauty and outdoor activities.
  • What outdoor activities are available at Kettle Moraine State Forest?
    • The forest features eleven designated-use trails that provide opportunities for:
      • Horseback riding
      • Hiking
      • Biking and mountain biking
      • Skiing and cross-country skiing
      • Snowshoeing
  • What is the Kettle Moraine Scenic Drive?
    • The Kettle Moraine Scenic Drive was designed to allow visitors from surrounding cities to experience the most beautiful scenery of the forest on a day trip.
  • What historical and natural landmarks are along the Kettle Moraine Scenic Drive?
    • The 115-mile drive passes by or near:
      • Four historical sites:
        • Wade House Stagecoach Inn
        • Holy Hill Basilica
        • Cushing Memorial Park
        • Old World Wisconsin Outdoor Museum
      • 24 natural areas
      • Numerous geological landmarks
      • 17 small Wisconsin communities

N1765 Highway G, Campbellsport, WI, Phone: 262-626-2116

4. Lake Geneva (1 hour 40 minutes)


See waterfront mansions and enjoy a romantic boat ride with couples.

Lake Geneva (1 hour 40 minutes)

© Lake Geneva

  • Why should Chicagoans visit Lake Geneva?
    • Chicagoans may wonder why they should leave Lake Michigan for Lake Geneva, but the two experiences are worlds apart. Lake Geneva is a Wisconsin resort city on the shores of a small lake by the same name.
  • What is the historical significance of Lake Geneva?
    • Lake Geneva is where wealthy Chicagoans came to build their mansions during the Gilded Age, making it a retreat for the elite.
  • How can visitors explore the mansions of Lake Geneva?
    • You can walk or bike the 21-mile shoreline along the Lake Geneva Shore Path for an up-close view of these historic mansions.
    • Another option is to see them from the water with the Lake Geneva Cruise Line, offering a unique perspective of the lake and its estates.
  • What activities can visitors enjoy in Lake Geneva?
    • This year-round getaway offers an eclectic mix of shops, restaurants, nightlife, and outdoor activities.

5. Naperville (40 minutes)


Explore riverwalk shops and relax in charming parks on a quick getaway.

Naperville (40 minutes)

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  • What makes Naperville a great day trip destination?
    • Besides Naperville’s small-town charm, the best reason for a visit is the Riverwalk, the city’s 1.75-mile walkway along the DuPage River.
  • What are the highlights of Naperville’s Riverwalk?
    • The Riverwalk features Moser Tower, a beautiful 158-foot bell tower, as well as a clock tower, three fountains, a covered bridge, and heritage sculptures.
    • Visitors can also enjoy an amphitheater, a labyrinth, and take out paddle boats for a scenic ride on the river.
  • What is Centennial Beach and Grill?
    • The Centennial Beach and Grill is a sandy beach waterpark and restaurant, making it a popular spot for relaxation and family fun.

6. Village of Oak Park (15 minutes)


Tour historic homes and discover local art on a short trip.

Village of Oak Park  (15 minutes)

© Village of Oak Park

  • What makes Oak Park unique?
    • Oak Park is a self-described village of free-thinking rebels and risk-takers. The community takes pride in its racial, cultural, ethnic, professional, religious, and socio-economic diversity.
  • Is Oak Park a welcoming community?
    • In other words, everyone is welcome in Oak Park, making it a vibrant and inclusive destination.
  • What historical attractions are in Oak Park?
    • History buffs will enjoy a walking tour of the Wright District, an area featuring prairie-style homes designed by Frank Lloyd Wright. Visitors can also tour his personal home and studio.
  • What other attractions does Oak Park offer?
    • Visitors may also enjoy the Oak Park Conservatory and the Brookfield Zoo.
    • The village boasts numerous independent shopping boutiques, a robust culinary scene, and a popular Saturday farmers’ market.

7. Six Flags Great America (1 hour)


Ride thrilling coasters and splash in the water park with kids.

Six Flags Great America (1 hour)

© Six Flags Great America

  • What is Six Flags Great America?
  • When is Six Flags Great America open?
    • The Gurnee location operates from the last weekend of April through the first weekend of November.
  • What kind of rides are at Six Flags Great America?
    • The park features 17 thrill rides, including 14 roller coasters.
    • There are also 23 family-friendly rides and 17 rides specifically designed for kids.
  • What food options are available at the park?
    • Visitors can enjoy a wide variety of food at over 50 restaurants and food stands.
  • What is Hurricane Harbor?
    • Hurricane Harbor is the park’s 20-acre water park with 30 attractions, including:
      • Surf simulators
      • Water slides
      • River floats
      • Children’s water playgrounds
      • A 14,000-square-foot family pool
    • It is open from Memorial Day weekend through Labor Day weekend.

1 Great America Parkway, Gurnee, IL, Phone: 847-249-1776

8. North Utica (1 hour 45 minutes)


Discover small-town charm and hike near waterfalls during fall.

North Utica (1 hour 45 minutes)

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  • What is North Utica known for?
    • North Utica is a sleepy river town along the Illinois-Michigan Canal and the Illinois River. It is a great destination for antique, wine, and nature lovers.
  • What shopping opportunities are available in North Utica?
    • Visitors will find wineries and wine shops, as well as antique stores, flea markets, rustic furniture and collectibles shops, and a pottery studio.
  • Where can visitors learn about North Utica’s history?
    • The LaSalle County Historical Museum provides insights into the town’s rich history.
  • What dining options are available in North Utica?
    • Popular eateries include Cajun Connection and Canal Port Bar & Grill.
  • What does Grand Bear Resort offer?
    • Grand Bear Resort offers inexpensive day passes to its 24,000-square-foot indoor waterpark. The resort also features a restaurant, a sports bar, and a sweet shop.
  • What outdoor activities are available near North Utica?
    • The area is home to four nearby state parks, providing plenty of outdoor recreational opportunities.

9. Chicago Botanic Garden (35 minutes)


Admire blooming gardens and walk along peaceful trails in spring.

Chicago Botanic Garden (35 minutes)

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  • What is the Chicago Botanic Garden?
    • Chicago Botanic Garden is home to over 30 distinct gardens, each designed with purposeful planning and unique aesthetics.
  • What types of gardens can visitors explore?
    • Visitors can enjoy the well-manicured Crescent and Heritage gardens, or experience the naturalistic style of the Lakeside and Native Plant gardens.
    • With such a wide range of gardens, choosing a favorite is a highly personal decision.
  • Are there self-guided tours available?
    • Yes, the botanical garden offers self-guided walking tours that are narrated via a smartphone app.
  • What attractions are available for families with children?
    • Families may want to visit the Nature Play Garden and the Children’s Growing Garden for a fun and educational experience.
  • What other activities are available at the Chicago Botanic Garden?
    • Guests can explore bike trails and rent bikes, participate in birding classes, and enjoy birdwatching.
    • The garden also features an onsite restaurant and a gift shop for visitors to enjoy.

1000 Lake Cook Road, Glencoe, IL, Phone: 847-835-5447

10. Indiana Dunes National Lakeshore (1 hour)


Hike sandy dunes and swim in Lake Michigan during summer.

Indiana Dunes National Lakeshore (1 hour)

© S Quintans/stock.adobe.com

  • What is Indiana Dunes National Lakeshore?
  • What outdoor activities can visitors enjoy?
    • The park features 50 miles of diverse trails where visitors can hike, bike, ride on horseback, snowshoe, cross-country ski, or birdwatch.
  • What are some must-see attractions besides the beaches?
    • Visitors can participate in interpretive programs and join ranger-led walking tours.
    • Families will enjoy the children’s outdoor Nature Play Zone at the Paul H. Douglas Center.
    • History enthusiasts can explore four historical buildings from a 19th-century homestead.
    • The park also features a 3,500-square-foot modern pavilion for visitors to relax and enjoy.
  • What is a must-do experience at Indiana Dunes?
    • Every trip should include a hike up West Beach’s Succession Trail, where visitors can take in an epic view of the Chicago skyline.

1100 N. Mineral Springs Road, Porter, IN, Phone: 219-395-1882

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